Diethylene Glycol → HCID 57970191, compound

HRID 1666695Notes

Reaction equation

HRID 1666695 reaction equation
Cl[C:2]1[CH:7]=[C:6]([C:8]([F:11])([F:10])[F:9])[CH:5]=[C:4]([CH3:12])[N:3]=1.[CH2:13]([N:20]1[CH2:24][CH2:23][C@H:22]([NH2:25])[CH2:21]1)[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1.C(O)COCCO.C(N(CC)C(C)C)(C)C>C(OCC)(=O)C.O>[CH2:13]([N:20]1[CH2:24][CH2:23][C@H:22]([NH:25][C:2]2[CH:7]=[C:6]([C:8]([F:11])([F:10])[F:9])[CH:5]=[C:4]([CH3:12])[N:3]=2)[CH2:21]1)[C:14]1[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=1

Participants

7

Reactant 4

HCID 8117Diethylene GlycolHCID 81531DiisopropylethylamineHCID 1519353(3S)-(+)-1-Benzyl-3-aminopyrrolidineHCID 27366262-Chloro-6-methyl-4-(trifluoromethyl)pyridine

Product 1

HCID 57970191HCID 57970191, compoundYield 24.4%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
140 °C

Procedure

A mixture of 2-chloro-6-methyl-4-trifluoromethylpyridine (0.196 g), (S)-1-benzyl-3-aminopyrrolidine (0.529 g), diethylene glycol (4 mL), and N,N-diisopropylethylamine (0.52 mL) was heated at 140° C. for 2 h using a microwave reaction apparatus. After completion of the reaction, water and ethyl acetate were added to the reaction solution, the mixture was extracted with ethyl acetate, washed with saturated brine, and then dried with anhydrous magnesium sulfate, then the desiccant was removed by filtration, and then the crude product obtained by concentration under reduced pressure was purified by silica gel column chromatography (silica gel, hexane/ethyl acetate=5:1-2:1) to obtain (S)-N-(1-benzylpyrrolidin-3-yl)-6-methyl-4-trifluoromethylpyridin-2-amine (0.082 g).

Workup

  1. customa microwave reaction apparatus
  2. additionwere added to the reaction solution
  3. extractionthe mixture was extracted with ethyl acetate
  4. washwashed with saturated brine
  5. dry with materialdried with anhydrous magnesium sulfate
  6. customthe desiccant was removed by filtration
  7. customthe crude product obtained by concentration under reduced pressure
  8. customwas purified by silica gel column chromatography (silica gel, hexane/ethyl acetate=5:1-2:1)

Sources & evidence

ORD record
ord-df0dc02cf1a34c1096c54260fd9d2e96
Source dataset
uspto-grants-2011_10
Patent number
US08044068B2

Reaction notes

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